Cottage holiday rentals in The Villages

4.95 out of 5 average rating, 157 reviews

A charming cottage exterior is showcased, featuring a welcoming porch adorned with potted plants. The lush green lawn surrounds the home, with a large tree providing shade. A fenced area is seen in the background, enhancing the outdoor space.

Cottage in Umatilla

Cozy & Quaint Little Cottage for Big Hearts!

❤️Near to springs and Manatee watch areas, Ocala Forest, Fishing🎣 equestrian🐎 activities, Mount Dora &🪑Antiques Markets. Just 39 miles to Orlando - Disney & 43 miles to the beach 🏖 🏡You’ll wake up in one of the last true Florida cottages, built in wood with heart and time.❤️A truly quaint cottage for a joyful stay. Entire Place! Pet Friendly! Free Parking! 2 bedrooms + 2 full baths! Original wood floor in master bedroom and Kitchen! No carpet floors! Nice quiet, safe neighborhood!☀️🌳

4.97 out of 5 average rating, 203 reviews

Cottage in Coleman

Romantic Escape on Peaceful Mini Farm

Escape to a peaceful private farm cottage just minutes from Villages. Enjoy a romantic, cozy retreat with a private fenced courtyard, mini farm charm, and thoughtful comforts throughout. Pets are welcome with no surprise fees. Easy self check-in and simple checkout make your stay stress-free. Close to Brownwood, dining, shopping, and I-75. Extra parking may be available for boats, trailers, or larger vehicles with advance notice. Traveling with family or friends? Ask about nearby sister rentals.

A well-appointed sleeping area features a white bed frame with plush bedding in navy and white tones. Two bedside tables with navy blue lamps flank the bed. Decorative pillows, including a map-themed cushion, add interest, while framed botanical prints hang above the headboard.

4.98 out of 5 average rating, 201 reviews

Charming Mount Dora Cottage • Walk to Downtown

Walking distance to all Downtown Mount Dora has to offer! Our lovely 2 bedroom, 1 bath 1940s cottage has been recently renovated. Features fully outfitted kitchen, deck with gas grill and outdoor firepit. Comfortable and elegant living space with 65 inch smart TV. Primary bedroom features King bed and smart tv. Second bedroom has two cozy twin beds. Bikes available for use. Whether you’re coming to relax, boat, shop or partake in one of Mount Dora's many festivities, consider staying here!

4.99 out of 5 average rating, 148 reviews

The exterior of a two-story detached home is presented, featuring white siding and black shutters. The entrance is adorned with planters, and a small walkway leads to the front door. Lush greenery surrounds the property, and a clear blue sky is visible above.

Cottage in Umatilla

Cottage by the Lake

Cute, comfortable 1935 detached home is 900 SQUARE FEET AND PET FRIENDLY. Walking distance to the Palm Mansion venue and 1.2 miles from Lakeview Gardens Venue. Main home’s on other side of property. Cottage is newly remodeled and fenced in. Views of Lake Umatilla from all rooms. 8 miles to beautiful Mount Dora and 3 miles to downtown Eustis. 1 hour to attractions, airport and east coast beaches. We are 20-30 minutes from most local Springs. Lake Umatilla does have public boat ramp access

4.91 out of 5 average rating, 117 reviews

A wooden dock extends into the calm waters, surrounded by lush greenery and mature trees. Steps lead up from the dock to a cottage nestled among the foliage, offering a serene and natural setting.

Cottage in Leesburg

Waterfront Cottage on The Harris Chain in Leesburg

Cozy waterfront cottage on Haynes Creek. Whether its relaxing, fishing from your own dock, boating the Harris chain, paddle boarding, birdwatching, use our kayaks or pedal boat, or exploring the nearby towns and springs... we have it all. Fully equip kitchen, outdoor grilling area, wifi and cable, parking, laundry, gas fire pit on your private deck, boat parking at your dock or book a tour with Monster Bass fishing. Walkable to nearby stores or Gator Bay for a drink, meal, or music!

A spacious living area features comfortable seating arrangements with soft furnishings and an open layout leading to a dining space. Natural light fills the room, complemented by warm, neutral tones and accents of greenery seen through the windows.

4.96 out of 5 average rating, 156 reviews

1 min walk 2 Downtown!Golf Cart Rental Pickle Ball

Enjoy a stylish experience in the HEART of Downtown Mount Dora! This gorgeous historic 1925 cottage is just a short 1 -minute walk to the main shopping and dining district of Mount Dora! You are a 1 minute walk to Mount Dora’s beautiful pickle ball courts! This beautifully decorated 1000 square foot - 5 Star rental has been recently updated to reflect its old Florida cottage feel. With all of the thoughtful touches you will be sure to enjoy a comfortable stay in this beautiful city.

4.96 out of 5 average rating, 112 reviews

Cottage in Ocklawaha

Cottage Americana at Coco Ranch

We are a pet friendly Cottage bring your furry friend and enjoy the cozy and playful place This is a family wood gated compound. Each Cottage are private, surrounded by beautiful comun areas. If your planing to get away from the city and connect with nature🦌🌳🐄 this is the perfect place. Surrounded by a lot of natural springs 💦 🍃 and also the convenients of local restaurants like “Gators Joes Beach Bar & Grill”🍽 at just 6m walk, 6m walk to Lake Weir, and more.

4.95 out of 5 average rating, 117 reviews

A charming cottage is showcased, featuring a light-colored exterior with red shutters. The entrance is framed by a covered porch and planters, while a landscaped area with low shrubs and flowers adds a welcoming touch to the pathway.

Cottage in Eustis

Anneliese's Cottage

Just a delightful walk from Lake Eustis and its quaint downtown shopping & dining district, a 10 minute drive to Historic downtown Mt. Dora, and less than an hour from Orlando / Daytona Beach, this cottage , decorated with cozy elegance, is the perfect place to relax and truly enjoy all that the area has to offer. Right next door, you'll find an eclectic day spa, where you can set up a relaxing massage, facial, or have your hair & nails done during your stay!

4.89 out of 5 average rating, 146 reviews

Four red Adirondack chairs are positioned on a grassy area, facing a calm body of water lined with lush trees. The sun casts long shadows, creating a serene and inviting outdoor space.

Cottage in Inverness

Sweetwater Cottage private dock, canoe & kayaks

FL is currently in the worst drought since 2012, water levels are 8ft + lower than normal and chains are dry. Come enjoy our lakeside cottage and its fun relaxing vibe! This private home is fully fenced and features a private dock. We are pet friendly for well behaved four legged friends that enjoy traveling. We have a 14 ft canoe and 2 kayaks for you to enjoy. We do have a small gas motor you can rent for the canoe allowing you to truly explore the lakes.

Superhost

A comfortable living area is highlighted by a spacious sectional sofa with decorative cushions. A ceiling fan and overhead lights provide ambient lighting. A large television is mounted on the wall opposite, while a patterned rug adds color to the wooden floor.

4.89 out of 5 average rating, 128 reviews

Refreshing 1930s Cottage in Mount Dora

Enjoy this refreshed cottage, originally built in 1931, located in the historic district and within walking distance to downtown Mount Dora. The cottage is equipped with queen and king beds, full kitchen, fire pit, smart TVs, outdoor patio, enclosed porch, washer/dryer, and private driveway. Take in the historic sites and homes nearby, beautiful lakes, boardwalk, lighthouse as well as all the shopping, dining, and entertainment downtown has to offer.

4.92 out of 5 average rating, 141 reviews

Cottage in Clermont

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

A cozy dining area is illuminated by natural light from windows on three sides. A blue table is surrounded by four wooden chairs, and a woven pendant light hangs above. Decorative elements include a bowl of fruit on the table, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 150 reviews

Walk to Downtown! - The Happy Hour Cottage

The Happy Hour Cottage is a newly renovated 1600 SF, 2 bedroom/1 bath unit. Located within walking distance to downtown, the marina, several parks, and Lake Dora. Enjoy the quaint neighborhoods, dining, shopping, or attend one of the year round festivities. Relax and enjoy the nostalgia of yesteryear while exploring downtown or relaxing in the courtyard with a glass of wine around the firepit.

Popular amenities for cottage rentals in The Villages

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A sunroom features large windows that provide expansive views of the landscape. A round glass dining table is surrounded by chairs, and a cozy armchair is positioned nearby. Natural light brightens the space, enhancing the inviting atmosphere.

Cottage in Lady Lake

Golf-Front Hilltop Cottage in The Villages!

A spacious living area features a light-colored sofa and two accent chairs, arranged around a woven area rug. Large windows allow natural light to fill the room, showcasing a view of the serene outdoors. Hardwood floors extend throughout the space.

Cottage in Yalaha

4.83 out of 5 average rating, 77 reviews

3BR/2BA Charming 1920's Lakefront Estate + Hot Tub

A charming single-story cottage is presented, featuring a front porch with a railing and two white chairs. The exterior showcases a light-colored facade with a sloped roof. Lush green grass and landscaped shrubs surround the cottage, contributing to a tranquil outdoor setting.

Cottage in Weirsdale

Villa 2928

4.98 out of 5 average rating, 45 reviews

Cozy Lake Cottage w/ Hot Tub + Boat Parking

A single-story house is surrounded by a white picket fence and lush green landscaping. A wide porch with steps leads to the entrance, framed by two greenery-filled trees. The building has light-colored siding, which contrasts with the bright blue sky and scattered clouds.

The Almond Cottage

The Pecan Cottage

Shangrila

Cottage in The Villages

5 out of 5 average rating, 6 reviews

Guest House- 1/1 Suite w/ Pool Use & Golf Cart!

Pet-friendly cottage rentals

A cozy sleeping area features a spacious bed with neutral bedding, complemented by wooden beams overhead. Two rocking chairs are positioned nearby, and a dresser provides additional storage. Natural light enters through a window with a light-filtering shade, creating a calming environment.

5 out of 5 average rating, 7 reviews

Cottage 34: Coconut Cottage | Dora Canal Court

4.95 out of 5 average rating, 95 reviews

A spacious fenced yard of three acres is visible, featuring a paved pathway leading up to a cozy home. Lush greenery surrounds the area, providing ample space for pets to roam freely. The structure showcases a welcoming entrance with a wooden deck.

Cottage in Summerfield

Private Dog Park | 4mi to Lake/Beach | Legends Run

The entrance of the cottage features a bright blue door framed by a covered porch. Colorful butterfly decorations adorn the light blue exterior walls, complemented by a welcome sign and a vibrant butterfly flag. Greenery and flowerbeds add to the inviting atmosphere.

4.98 out of 5 average rating, 53 reviews

Villa Mariposa 🦋 in the heart of Mt Dora

A spacious living area features high ceilings with exposed wooden beams and a chandelier. Various seating options, including a dark sofa and striped chairs, surround a coffee table on a large area rug. Natural light filters through large windows in the background.

4.95 out of 5 average rating, 42 reviews

Unique cottage with a heated pool on the canal

4.85 out of 5 average rating, 41 reviews

The exterior view showcases a two-story cottage with a spacious pool in the foreground. The pool is surrounded by a concrete deck and features clear blue water. A large wooden deck is visible, providing access to the upper level of the cottage, complemented by lush greenery.

Cottage in Ocala

Springs Equestrian Lodge| Pool |Historic District

5 out of 5 average rating, 52 reviews

A bright sitting area features large windows allowing natural light to fill the space. Comfortable seating includes a light grey sofa and an additional couch, complemented by a coffee table. A charming blue accent table holds household items, while a kitchen area with modern appliances is visible in the background.

Cottage in Ocklawaha

Cozy Cottage At Lake Weir

4.95 out of 5 average rating, 42 reviews

A screened porch is framed by lush tropical foliage, including a banana plant and ferns. The entrance is marked by a stone pathway leading to a cozy seating area with a small table, inviting relaxation amid natural surroundings.

Cottage in Inverness

The Lake House at Dead Boat Cove

4.94 out of 5 average rating, 72 reviews

Cottage | Walk Downtown | Pet Friendly/Fenced Yard

Private cottage rentals

The exterior of a charming cottage is showcased, featuring light green siding and a welcoming front porch. Lush palm trees and manicured landscaping surround the home, while a white picket fence adds a quaint touch. The entrance is adorned with a decorative screen door.

5 out of 5 average rating, 29 reviews

"WOW Cottage" ~ A Legendary Can't-Miss Experience!

A single-story house is framed by well-maintained green lawns and mature trees. The structure features a welcoming porch with columns, and large windows are symmetrically placed on either side of the front door, allowing ample natural light to enter the home.

4.95 out of 5 average rating, 66 reviews

Lakeside Retreat

4.89 out of 5 average rating, 76 reviews

A view of the serene Lake Weir features lush green grass and vibrant yellow flowers in the foreground. Beyond, palm trees sway gently against a blue sky, while a wooden dock extends into the lake, enhancing the tranquil atmosphere.

Cottage in Summerfield

Lake Weir Retreat w/Dock The Villages/Ocala

A cozy living area features a soft sofa adorned with yellow cushions, paired with a vintage armchair. A wooden sideboard displays books and decorative elements, while a mounted flat-screen TV is positioned above. Natural light filters through window blinds, illuminating the warm oak flooring.

5 out of 5 average rating, 90 reviews

1/1 Cottage in Mount Dora's Historic District

4.85 out of 5 average rating, 92 reviews

A scenic outdoor area is featured, with a long picnic table positioned on a deck. Colorful chairs are arranged nearby, and water views extend into the distance, highlighting a sandy shore. Bright skies and green grass create an inviting setting.

Cottage in Summerfield

The Villages LakeFront Lake Weir Home

4.95 out of 5 average rating, 56 reviews

A charming cottage is positioned near the water, featuring a spacious patio with a dining table and chairs. A barbecue grill is on a stone pathway, with a clear view of the lake in the background and blue skies above, adding to the serene setting.

Cottage in Weirsdale

View of Lake Weir with a private beach

The bungalow is set amongst trees, featuring a welcoming front porch with rocking chairs. Soft lighting enhances the green exterior, and a mix of landscaping elements is present. A pathway leads to the front door, framed by decorative plants and the glow of nearby lights.

5 out of 5 average rating, 59 reviews

Orange Grove Cottage in Historic Downtown District

A sandy beach area is pictured alongside Lake Dora, featuring a row of six lounge chairs positioned under a green umbrella. A wooden dock extends into the lake, offering access to the water and enhancing the serene atmosphere.